Recent advances in catalytic synthesis of medium-ring lactones and their derivatives

In light of the ever-increasing significance of medium-sized lactones across the range of chemical sciences, this review summarizes the recent advances in catalytic synthesis of medium-ring lactones with emphasis on reaction scope and mechanism.

• Publication year

  2021

• Venue

  Catalysis science & technology

• Publication date

  2021-09-01

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1039/d1cy01438b
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

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  2021cited by this paper
• Ru-catalysed C(sp2)-H vinylation/annulation of benzoic acids and alkynes: rapid access to medium-sized lactones.

  2021cited by this paper
• 1-Alkoxyvinyl Ester as an Excellent Acyl Donor: Efficient Macrolactone Synthesis.

  2021cited by this paper
• NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines

  2021cited by this paper
• Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group.

  2021cited by this paper
• Easy access to medium-sized lactones through metal carbene migratory insertion enabled 1,4-palladium shift

  2020cited by this paper
• Palladium-catalysed cyclisation of vinylethylene carbonates and anhydrides: a new approach to diverse medium-sized bislactones.

  2020cited by this paper
• N-Heterocyclic Carbene-Based Catalysis Enabling Cross-Coupling Reactions

  2020cited by this paper
• Evaluating the Viability of Successive Ring‐Expansions Based on Amino Acid and Hydroxyacid Side‐Chain Insertion

  2020cited by this paper
• Palladium-Catalyzed Asymmetric [8+2] Dipolar Cycloadditions of Vinyl Carbamates and Photogenerated Ketenes.

  2020cited by this paper
• Synthesis of medium-sized lactones from siloxy alkynes via ring expansion

  2020cited by this paper
• Palladium-catalysed decarboxylative annulations of vinylethylene carbonates leading to diverse functionalised heterocycles.

  2020cited by this paper
• Modular Rhodium-Catalyzed Synthesis of Quinolines from Anthranils and Acrylic Acids

  2020cited by this paper
• Synthesis of Highly Functionalized 12-Membered Trifluoromethyl Heterocycles via a Nondecarboxylative Pd-Catalyzed [6 + 6] Annulation

  2020cited by this paper
• N-Heterocyclic Carbene Complexes in C-H Activation Reactions.

  2020cited by this paper
• Modular Synthesis of Medium-Sized Fluorinated and Nonfluorinated Heterocyclic Lactones by Sequential CN-Bond-Cleaving Ring Expansion under Pd Catalysis

  2020cited by this paper
• Photocatalytic Aerobic Oxidative Ring Expansion of Cyclic Ketones to Macrolactones via Cerium and Cyanoanthracene Catalysis.

  2020cited by this paper
• Exploitation of the New Reactivity of Vinylcyclopropanes for Palladium-Catalyzed, Asymmetric [5+2] Dipolar Cycloadditions.

  2020cited by this paper
• Construction of Medium-Sized Rings by Gold Catalysis.

  2020cited by this paper
• Synergetic iridium and amine catalysis enables asymmetric [4+2] cycloadditions of vinyl aminoalcohols with carbonyls

  2019cited by this paper
• Synthesis of 23-, 25-, 27-, and 29-Membered ( Z)-Selective Unsaturated and Saturated Macrocyclic Lactones from 16- and 17-Membered Macrocyclic Lactones and Bromoalcohols by Wittig Reaction, Yamaguchi Macrolactonization, and Photoinduced Decarboxylative Radical Macrolactonization.

  2019cited by this paper
• Nitrate-Mediated Alcohol Oxidation on Cadmium Sulfide Photocatalysts

  2019cited by this paper
• Strategies for the Diversity-Oriented Synthesis of Macrocycles.

  2019cited by this paper
• Internal nucleophilic catalyst mediated cyclisation/ring expansion cascades for the synthesis of medium-sized lactones and lactams.

  2019cited by this paper
• An Organoselenium Accelerated Bromolactonization Reaction.

  2019cited by this paper
• Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade.

  2019cited by this paper
• A photoinduced Wolff rearrangement/Pd-catalyzed [3+2] cycloaddition sequence: an unexpected route to tetrahydrofurans.

  2019cited by this paper
• Enantioselective Synthesis of Chiral Medium-Sized Cyclic Compounds via Tandem Cycloaddition/Cope Rearrangement Strategy

  2019cited by this paper
• Stereoselective Synthesis of Diverse Lactones through a Cascade Reaction of Rhodium Carbenoids with Ketoacids.

  2018cited by this paper
• Catalytic Transformations of Functionalized Cyclic Organic Carbonates.

  2018cited by this paper
• Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions

  2018cited by this paper
• Direct Photocatalytic Synthesis of Medium-Sized Lactams by C-C Bond Cleavage.

  2018cited by this paper
• Recent Advances in the Catalytic Cycloaddition of 1,n-Dipoles

  2018cited by this paper
• Metal-Free Catalyst for Visible-Light-Induced Oxidation of Unactivated Alcohols Using Air/Oxygen as an Oxidant

  2018cited by this paper
• Synthesis of Functionalized Biaryls and Poly(hetero)aryl Containing Medium-Sized Lactones with Cyclic Diaryliodonium Salts.

  2017cited by this paper
• N-Heterocyclic Carbene Catalysis via the α,β-Unsaturated Acyl Azolium

  2017cited by this paper
• Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

  2017cited by this paper
• Palladium‐Catalyzed Cyclization of Free Hydroxyalkenoic Acids: Regio‐ and Chemoselective Access to Methylene Lactones

  2017cited by this paper
• Ring-Expansion Approach to Medium-Sized Lactams and Analysis of Their Medicinal Lead-Like Properties.

  2017cited by this paper
• Enantioselective Medium-Ring Lactone Synthesis through an NHC-Catalyzed Intramolecular Desymmetrization of Prochiral 1,3-Diols

  2017cited by this paper
• Oxidative C-H/C-H Coupling Reactions between Two (Hetero)arenes.

  2017cited by this paper
• Using Singlet Oxygen to Synthesize Natural Products and Drugs.

  2016cited by this paper
• Organoselenium and DMAP co-catalysis: regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes.

  2016cited by this paper
• Enantioselective Rhodium-Catalyzed Atom-Economical Macrolactonization.

  2016cited by this paper
• Dual Catalysis Strategies in Photochemical Synthesis

  2016cited by this paper
• A Copper-Catalyzed Decarboxylative Amination/Hydroamination Sequence: Switchable Synthesis of Functionalized Indoles.

  2016cited by this paper
• Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

  2016cited by this paper
• Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

  2016cited by this paper
• Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization.

  2016cited by this paper
• Catalytic Asymmetric [4 + 1] Annulation of Sulfur Ylides with Copper-Allenylidene Intermediates.

  2016cited by this paper
• Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

  2015cited by this paper
• Synthesis of Strained 1,3-Diene Macrocycles via Copper-Mediated Castro-Stephens Coupling/Alkyne Reduction Tandem Reactions.

  2015cited by this paper
• The Synthesis of Structurally Diverse Macrocycles By Successive Ring Expansion.

  2015cited by this paper
• Palladium-Catalyzed Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Electrophiles: Construction of Quaternary Stereocenters

  2015cited by this paper
• Dual catalysis sees the light: combining photoredox with organo-, acid, and transition-metal catalysis.

  2014cited by this paper
• An overview of N-heterocyclic carbenes

  2014cited by this paper
• C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization.

  2013cited by this paper
• Synthesis of eight-membered lactones: intermolecular [6+2] cyclization of amphoteric molecules with siloxy alkynes.

  2012cited by this paper
• Biomimetic diversity-oriented synthesis of benzannulated medium rings via ring expansion

  2012cited by this paper
• Diversity-Oriented Synthesis Approach to Macrocycles via Oxidative Ring Expansion

  2012cited by this paper
• Enantioselective halocyclization using reagents tailored for chiral anion phase-transfer catalysis.

  2012cited by this paper
• Tandem cross-dimerisation/oxonia-cope reaction of carbonyl compounds to homoallylic esters and lactones.

  2012cited by this paper
• Efficient medium ring size bromolactonization using a sulfur-based zwitterionic organocatalyst.

  2012cited by this paper
• Assessing atropisomer axial chirality in drug discovery and development.

  2011cited by this paper
• Enantioselective bromoaminocyclization using amino-thiocarbamate catalysts.

  2011cited by this paper
• Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

  2011cited by this paper
• Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery.

  2011cited by this paper
• Metathesis in total synthesis.

  2011cited by this paper
• Palladium-catalyzed decarboxylative [4 + 3] cyclization of gamma-methylidene-delta-valerolactones with 1,1-dicyanocyclopropanes.

  2009cited by this paper
• Synthesis of Heterocycle-Annulated Medium-Sized Oxacycles and Lactone Derivative by Intramoleculer Heck Reaction

  2009cited by this paper
• Zwitterionic salts as mild organocatalysts for transesterification.

  2008cited by this paper
• Total synthesis of natural 8- and 9-membered lactones: recent advancements in medium-sized ring formation.

  2007cited by this paper
• Organic spirocyclic initiators for the ring-expansion polymerization of beta-lactones.

  2007cited by this paper
• Bicyclic β-Hydroxytetrahydrofurans as Precursors of Medium Ring Keto-Lactones

  2007cited by this paper
• Macrolactonizations in the total synthesis of natural products.

  2006cited by this paper
• Macrolactonization via hydrocarbon oxidation.

  2006cited by this paper
• Macrocyclization by ring-closing metathesis in the total synthesis of natural products: reaction conditions and limitations.

  2006cited by this paper
• Ring-closing metathesis approach to dictyostatin.

  2005cited by this paper
• Synthesis of medium- and large-sized lactones in an aqueous-organic biphasic system.

  2005cited by this paper
• Iodine electrophiles in stereoselective reactions: recent developments and synthetic applications.

  2004cited by this paper
• Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis.

  2004cited by this paper
• Direct, stereoselective substitution in [Rh(CO)(2)Cl](2)-catalyzed allylic alkylations of unsymmetrical substrates.

  2004cited by this paper
• An effective use of benzoic anhydride and its derivatives for the synthesis of carboxylic esters and lactones: a powerful and convenient mixed anhydride method promoted by basic catalysts.

  2004cited by this paper
• New sesterterpene metabolites from the Mediterranean sponge Cacospongia scalaris.

  2003cited by this paper
• Total synthesis of octalactin A via ring-closing metathesis reaction

  2002cited by this paper
• Total syntheses of the phytotoxic lactones herbarumin I and II and a synthesis-based solution of the pinolidoxin puzzle.

  2002cited by this paper
• New type sesquiterpene lactone from almond hulls (Prunus amygdalus Batsch)

  2002cited by this paper
• Evaluation of exo-endo Ratios in the Halolactonization of ω-Unsaturated Acids

  2001cited by this paper
• Synthesis of Functionalized Olefins by Cross and Ring-Closing Metatheses

  2000cited by this paper
• Metal-mediated synthesis of medium-sized rings.

  2000cited by this paper
• Diverse Methods for Medium Ring Synthesis

  1998cited by this paper
• SYNTHESIS OF MEDIUM RING ETHERS. 5. THE SYNTHESIS OF (+)-LAURENCIN

  1997cited by this paper
• Medium ring lactones

  1995cited by this paper
• Preparation of seven-membered and medium-ring lactones by iodo lactonization

  1993cited by this paper
• A Facile Procedure for Oxidative Cleavage of Enolic Olefins to the Carbonyl Compounds with Ruthenium Tetraoxide (RuO4).

  1986cited by this paper
• A facile procedure for oxidative cleavage of enolic olefins to the carbonyl compounds with ruthenium tetraoxide (RuO4)

  1985cited by this paper
• Ring closure reactions of bifunctional chain molecules

  1981cited by this paper
• Ring-closure reactions. 7. Kinetics and activation parameters of lactone formation in the range of 3- to 23-membered rings

  1977cited by this paper

• Biologically Active Natural δ‐Lactones in Medicinal Chemistry: Structures, Bioactivities, and Synthesis

  2026cites this paper
• Rhodium-Catalyzed Tandem Asymmetric Allylic Decarboxylative Addition and Cyclization of Vinylethylene Carbonates with N-Nosylimines

  2024cites this paper
• Stereodivergent synthesis of α-fluoro α-azaaryl γ-butyrolactones via cooperative copper and iridium catalysis

  2022cites this paper